Highly Regioselective Butylation of N‐Sulfonyl‐1,2,3‐triazoles by the Formation of Quaternary Carbon‐Centered C(sp3)─N Bonds
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DOI: 10.1002/ajoc.202500353
Abstract: An efficient example of quaternary carbon‐centered C(sp3)─N bond formation has been developed using N‐sulfonyl‐1,2,3‐triazoles and tert‐butyl hydroperoxide with a high regioselectivity in good yields (71%–83%) without any additional catalysts or additives. The unprecedented reaction was… read more here.
Keywords: centered sp3; carbon centered; sulfonyl triazoles; highly regioselective ... See more keywords
Palladium-Catalyzed Asymmetric Desymmetrization for the Simultaneous Construction of Chiral Phosphorus and Quaternary Carbon Stereocenters.
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DOI: 10.1021/acs.orglett.4c01863
Abstract: A palladium-catalyzed asymmetric tandem Heck and carbonylation of bisallyl-phosphine oxides has been developed. This desymmetrization process provided an efficient route to the simultaneous synthesis of a chiral P-stereogenic center and a chiral quaternary carbon stereocenter… read more here.
Keywords: catalyzed asymmetric; asymmetric desymmetrization; palladium catalyzed; quaternary carbon ... See more keywords
Palladium-Catalyzed Alkoxycarbonylation of Alcohols for the Synthesis of Cyclobutanecarboxylates with α-Quaternary Carbon Centers
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DOI: 10.1021/acs.orglett.5c00087
Abstract: A palladium-catalyzed alkoxycarbonylation with two different alcohols for the synthesis of cyclobutanecarboxylates bearing an α-quaternary carbon center is presented. The reaction utilizes readily accessible starting materials, tolerates a broad scope of functional groups, and provides… read more here.
Keywords: palladium catalyzed; alcohols synthesis; catalyzed alkoxycarbonylation; synthesis ... See more keywords
Construction of Vicinal Quaternary Carbon Centers via Cobalt-Catalyzed Asymmetric Reverse Prenylation.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.8b04030
Abstract: A highly enantioselective cobalt-catalyzed reverse prenylation of β-ketoester with tertiary allylic carbonate to construct vicinal all-carbon quaternary carbon centers has been developed. By using the cobalt/( S, S)Ph-BPE complex generated in situ with zinc reduction,… read more here.
Keywords: carbon; cobalt; reverse prenylation; carbon centers ... See more keywords
Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.9b02692
Abstract: We report the catalytic enantio- and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the… read more here.
Keywords: enantio diastereoselective; carbon; quaternary carbon; carbon stereogenic ... See more keywords
Pd-Catalyzed Allylic Alkylation of gem-Alkyl,Aryl-Disubstituted Allyl Reagents with Ketones: Diastereoselective Construction of Vicinal Tertiary and Quaternary Carbon Centers
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DOI: 10.1021/acscatal.7b04313
Abstract: (E)-gem-Alkyl,aryl-disubstituted allyl carbonates can react with ketones under Pd catalysis using a commercially available NHC ligand by suppressing the β-H elimination. Ketones with α-tertiary, β-quaternary carbon stereocenters were produced in high yields with high regio-… read more here.
Keywords: aryl disubstituted; tertiary quaternary; disubstituted allyl; quaternary carbon ... See more keywords
Structure and Properties of Poly-α-olefins Containing Quaternary Carbon Centers
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DOI: 10.1021/acsomega.9b04361
Abstract: In this paper, poly-α-olefins (PAO) containing quaternary carbon centers were prepared by two-step oligomerization using a metallocene catalyst followed by a Ziegler–Natta catalyst. First, the 1-decene dimer was oligomerized with [t-BuN(Me)2C(η5-C5H4)]ZrCl2, and the effects of… read more here.
Keywords: product; containing quaternary; carbon centers; quaternary carbon ... See more keywords
Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon.
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DOI: 10.1021/jacs.1c03454
Abstract: Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes… read more here.
Keywords: hydroaminocarbonylation disubstituted; quaternary carbon; catalyzed markovnikov; hydroaminocarbonylation ... See more keywords
Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters
Sign Up to like & getrecommendations! Published in 2022 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.2c01695
Abstract: Organoaluminum species promote a smooth nucleophilic substitution at the quaternary carbon stereocenter of stereodefined polysubstituted cyclopropyl methyl phosphate with a complete inversion of configuration, even when more reactive functional groups are present. The regio- and… read more here.
Keywords: carbon; quaternary carbon; carbon stereocenters; stereocenters quaternary ... See more keywords
Quaternary Carbon Editing Enabled by Sequential Palladium Migration.
Sign Up to like & getrecommendations! Published in 2024 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c07706
Abstract: Peripheral functionalization of a quaternary carbon via C(sp3)-H bond activation has made significant progress in recent years. However, direct editing of a quaternary carbon through Csp3-Csp3 bond cleavage and refunctionalization of nonstrained acyclic molecules remain… read more here.
Keywords: carbon editing; carbon; migration; bond ... See more keywords
Facile Access to Quaternary Carbon Centers via Ni-Catalyzed Arylation of Alkenes with Organoborons.
Sign Up to like & getrecommendations! Published in 2025 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.4c17313
Abstract: Quaternary carbon centers are widespread structural motifs, thus representing extensive interest in organic synthesis. We describe here an efficient nickel-catalyzed intermolecular, Markovnikov-selective arylation of minimally functionalized alkenes with stable organoborons, affording a broad range of… read more here.
Keywords: carbon; facile access; carbon centers; arylation ... See more keywords